Clean synthesis of a-bromo ketones and their utilisation in the synthesis of 2-aIkoxy-2,3-dihydro-2-aryl-l,4-benzodioxanes, 2-amino-4-aryI-l,3-thiazoles and piperidino-2-amino-l,3-thiazoles using polymer-supported reagents

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 17, 1999, Pages 2425-2427

  Habermann, Jörg ^a   Ley, Steven V ^a   Scicinski, Jan J ^a   Scott, James S ^a   Smits, René ^a   Thomas, Andrew W ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000196260     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a905616e     Document Type: Article

References (37)

1. (a) B. Hinzen and S. V. Ley, J. Chem. Soc., Perkin Trans, l, 1998, 1;
2. (b) F. Haunert, M. H. Bolli, B. Hinzen and S. V. Ley, J. Chem. Soc., Perkin Trans, l, 1998, 2235;
3. S. V. Ley, M. H. Bolli, B. Hinzen, A.-G. Gervois and B. J. Hall, J. Chem. Soc., Perkin Trans. J, 1998, 2239;
4. M. H. Bolli and S. V. Ley, J. Chem. Soc., Perkin Trans, l, 1998,2243;
5. (e)J. Habermann, S. V. Ley and J.S.Scott, J. Chem. Soc, Perkin Trans, l, 1998, 3127;
6. (f) M. Caldarelli, J. Habermann and S. V. Ley, J. Chem. Soc., Perkin Trans, l, 1999, 107;
7. (g) S. V. Ley, A. W. Thomas and H. Finch, J. Chem. Soc., Perkin Trans, l, 1999, 669;
8. (h) M. Caldarelli, J. Habermann and S. V. Ley, Bioorg. Med. Chem. Leu., 1999,9,2049.
9. S. V. Ley, O. Schucht, A. W. Thomas and P. J. Murray. J. Chem. Soc, Perkin Trans. J, 1999, 1251.
10. J. Habermann, S. V. Ley and J. S. Scott, J. Chem. Soc., Perkin Trans. I, 1999,1253.
11. (a) S. S. Nikam, A. R. Martin and D. L. Nelson, J. A fed. Chem., 1988, 31, 1965;
12. (b) D. L. Nelson and E. W. Taylor, Eur. J. Pharmac öl., 1986,124,207.
13. (a) J. C. Doxey, A. G. Roach, D. A. Strachan and N. K. Virdee, Br. J. Pharmacol., 1984, 83, 713;
14. (b) J. C. Doxey, A. G. Roach and C. F. C. Smith, Br. J. Pharmacol., 1984, 83, 489.
15. C. B. Chapelo, P. L. Myers, R. C. M. Butler, J. C. Doxey, A. G. Roach and C. F. C. Smith, J. Med. Chem., 1983,26, 823.
16. L. Lalloz, V. Loppinet, G. Coudert, G. Guillaumet, B. Loubinoux, C. Labrid, M. Beaughard, G. Dureng and J. C. Lamer, J. Med. Chem., 1981,24,994.
17. H. Jan, W. Wouter and I. V. Wijngaarden, EP 138 880/1985 (Chem. Abstr., 1985,103, 123520).
18. (a) I. B. Dzvinchuk, E. F. Granin, M. O. Lozinskii and L. P. Charuiskaya, Fklol. Akt. Veshchestva., 1988, 20, 66 (Chem. Abstr., 1989,110,19754);
19. (b) I. B. Dzvinchuk and M. O. Lozinskii, Zh. Org. Khim., 1988, 24, 2167 (Chem. Abstr., 1988, 110, 231011);
20. I. B. Dzvinchuk, S. V. Serada, M. O. Lozinskii and Y. T. Struchkov, Zh. Org. Khim., 1991,27, 1058 (Chem. Abslr., 1991,116, 6001);
21. I. B. Dzvinchuk and M. O. Lozinskii. Kliim. Geterotsikl. Soedin., 1985, 1570 (
22. Chem. Abstr., 1985, 105, 78884);
23. (e) I. B. Dzvinchuk and M. O. Lozinskii, Zh. Org. Khim., 1991, 27, 649 (Chem. Abstr., 1991, 115,207278).
24. M. R. Stillings, C. B. Chapleo, R. C. M. Butler, J. A. Davis, C. D. England, M. Myers, P. L. Myers, N. Tweddle, A. P. Welbourn, J. C. Doxey and C. F. C. Smith, J. Med. Cliem., 1985, 28, 1054; and references cited within.
25. S. Xi, M. Tao, W. Chen and J. Gao, Nanjing Daxue Xuebao, Ziran Kexue., 1989,25,638
26. (Chem. Abstr., 1991,114,101260).
27. The preparation of 2,2-disubstituted-l,4-benzodioxanes was realised by the reaction of a-bromo ketones with catechol in a methanolic solution of triethylamine or in the presence of silver powder and potassium iodide. During the progress of our investigations, an improved synthesis of 2-hydroxy-2-aryl-l,4-benzodioxanes was reported: T. Ganesh, C. Harish Kumar and G. L. D. Krupadanam, Synth. Commun., 1999,29,2069.
28. l Habermann, R. Smits and S. V. Ley, J. Chem. Soc, Perkin Trans. 1,1999, accompanying paper 9/04384E. Polymer-supported pyridinium perbromide (3.0 mequiv. Br," g~') was used as purchased from Aldrich.
29. Macroporous triethylammonium methylpolystyrene carbonate resin ('carbonate on polystyrene' 2.6 mmol g"1) was purchased from Argonaut Technologies. Prior to use the resin was thoroughly washed with dry methanol and then dried overnight in vacua.
30. + form, 1.0 g) for 6 h, the closed-chain 2-hydroxy-2-aryl-l,4-benzodioxanes 4a-f were the only products obtained. In some cases the pharmacologically active form was found to be the open-chain tautomer, e.g. the phytotoxic form as fungicides [réf. 9(a)]; or the closed-chain tautomer, e.g. the blood-pressure lowering benzodioxane derivatives (réf. 8). Systematic surveys of the electronic effects of substitents on the 2-aryI ring on the ring-chain tautomerism have been reported [réf. 9(b}-(e)].
31. (a) K. C. Nicolaou, F. Roschangar and D. Vourloumis, Angew. Chem., Int. Ed., 1998, 37, 2015 and references cited within;
32. (b) M. Sefkow and G. Höfle, Heterocycles, 1998, 48, 2485. In this paper a PEG-supported Burgess reagent was used for the cyclodehydration of β-hydroxy thioamides to afford 1,3-thiazoIes;
33. S. V. Downing, E. Aguilar and A. I. Meyers, X Org. Chem., 1999, 64, 826;
34. P. Wipf, Chem. Rev., 1995, 95,2115.
35. K. Yamaguchi, M. Yada, T. Tsuji, Y. Hatanaka, K. Goda and T. Kobori, Bioorg. A fed. Chem. Lett., 1999,9,957.
36. W. Xu, R. Mohan and M. M. Morrissey, Tetrahedron Lett., 1997, 38,7337.
37. The cycloaddition of 2b,c,i with thiourea 9 required heating in refluxing THF for 24 h. The formation of aminothiazoles 8e,f could also be effected by stirring at room temperature for 15 minutes in acetonitrile.